- Chemoselective reduction of ?,¢-unsaturated carbonyl and carboxylic compounds by hydrogen iodide
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The selective reduction of ?,¢-unsaturated carbonyl compounds was achieved to produce saturated carbonyl compounds with aqueous HI solution. The introduction of an aryl group at an ? or ¢ position efficiently facilitated the reduction with good yield. The reaction was applicable to compounds bearing carboxylic acids and halogen atoms. Through the investigation of the reaction mechanism, it was found that Michael-type addition of iodide occurred to produce ¢-iodo compounds followed by the reduction of C-I bond via anionic and radical paths.
- Matsumoto, Shoji,Marumoto, Hayato,Akazome, Motohiro,Otani, Yasuhiko,Kaiho, Tatsuo
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p. 590 - 599
(2021/03/29)
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- Fluorescent Molecular Logic Gates Driven by Temperature and by Protons in Solution and on Solid
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Temperature-driven fluorescent NOT logic is demonstrated by exploiting predissociation in a 1,3,5-trisubstituted Δ2-pyrazoline on its own and when grafted onto silica microparticles. Related Δ2-pyrazolines become proton-driven YES an
- West, Matthew E. S.,Yao, Chao-Yi,Melaugh, Gavin,Kawamoto, Kyoko,Uchiyama, Seiichi,de Silva, A. Prasanna
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supporting information
p. 13268 - 13274
(2021/08/06)
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- Synthesis and structure-activity relationship of new chalcone linked 5-phenyl-3-isoxazolecarboxylic acid methyl esters potentially active against drug resistant Mycobacterium tuberculosis
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In search of novel therapeutic agents active against emerging drug-resistant Mycobacterium tuberculosis and to counter the long treatment protocol of existing drugs, herein we present synthesis and biological evaluation of a new series of 5-phenyl-3-isoxazolecarboxylic acid methyl ester-chalcone hybrids. Among 35 synthesized compounds, 32 analogues displayed potent in-vitro activity against Mycobacterium tuberculosis H37Rv with MIC 0.12–16 μg/mL. Cell viability test against Vero cells indicated 29 compounds to be non-cytotoxic (CC50 > 20 μg/mL & SI > 10). Most potent compounds with MIC 0.12 μg/mL (7 b, 7j, 7 ab) exhibited selectivity index (SI) in excess of 320. Further studies on activity against drug-resistant Mycobacterium tuberculosis revealed 7j as the most potent compound with MIC 0.03–0.5 μg/mL. Time-kill kinetic study suggested compound 7j displaying concentration-dependent bactericidal killing activity with relatively comparable potency to that of current first-line anti-TB drugs. Taken together, 7j presents a novel hit with potential to be translated into a potent antimycobacterial.
- Sahoo, Santosh Kumar,Rani, Bandela,Gaikwad, Nikhil Baliram,Ahmad, Mohammad Naiyaz,Kaul, Grace,Shukla, Manjulika,Nanduri, Srinivas,Dasgupta, Arunava,Chopra, Sidharth,Yaddanapudi, Venkata Madhavi
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- Microwave-assisted Synthesis and Molecular Docking Study of Heteroaromatic Chalcone Derivatives as Potential Antibacterial Agents
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In this study, a series of chalcone derivatives (1a–c) were synthesized via Claisen-Schmidt condensation, followed by aza-Michael addition to form pyrazoline derivatives (2a–c and 3a–c). The reaction was performed via microwave radiation to give excellent
- Farooq, Saba,Mortadza, Nur Arif,Ngaini, Zainab
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supporting information
(2020/09/09)
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- A chalcone derivative binds a putative allosteric site of YopH: Inhibition of a virulence factor of Yersinia
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Identification of allosteric inhibitors of PTPs has attracted great interest as a new strategy to overcome the challenge of discover potent and selective molecules for therapeutic intervention. YopH is a virulence factor of the genus Yersinia, validated a
- Botta, Maurizio,Domeneghini Chiaradia-Delatorre, Louise,Menegatti, Angela C. O.,Mori, Mattia,Nunes, Ricardo J.,Rocha, Ruth F.,Sens, Larissa,Terenzi, Hernán,Tizziani, Tiago,de Souza, Ana C. A.,de Souza, Luiz F. S.
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supporting information
(2020/06/25)
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- CYCLOADDITION REACTIONS USING QUANTUM DOTS
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Disclosed herein are methods in which colloidal quantum dots (QDs) can serve as visible-light chromophores, photocatalysts, and reusable scaffolds for homo- and hetero-intermolecular [2+2] photocycloadditions. The methods may lead to >90% tunable regiosel
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Paragraph 0131-0132
(2020/11/30)
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- Synthesis of Kojic Ester Derivatives as Potential Antibacterial Agent
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The search for lead product with beneficial pharmacological properties has become a great challenge and costly. Extraction and synthetic modification of bioactive compounds from natural resources has gained great attention and is cost effective. In this study, kojic acid was produced from fungal fermentation, using sago waste as substrate, and chemically incorporated with chalcones and azobenzene to form a series of kojic ester derivatives and evaluated for antibacterial activities. Kojic ester bearing halogenated chalcone demonstrated active inhibition against Staphylococcus aureus compared to that of standard ampicillin. The inhibition increased as the electronegativity of halogens decreased, while incorporation of azobenzene derivatives on kojic acid backbone demonstrated fair antibacterial activity against Escherichia coli with minimum inhibitory concentration (MIC) of 190-330 ppm. The presence of C=C and N=N reactive moieties in both chalcone and azo molecules contributed to the potential biological activities of the kojic acid ester.
- Sie, Carolynne Zie Wei,Ngaini, Zainab,Suhaili, Nurashikin,Madiahlagan, Eswaran
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- Novel 1,3,4-thiadiazole-chalcone hybrids containing catechol moiety: synthesis, antioxidant activity, cytotoxicity and DNA interaction studies
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Hybrid compounds that combine the 1,3,4-thiadiazole-containing catechol moiety with a chalcone motif were synthesized and examined for their antioxidant activity, cytotoxicity, and DNA-binding activity. A series of thirteen compounds showed strong antioxi
- Jakovljevi?, Katarina,Joksovi?, Milan D.,Mati?, Ivana Z.,Petrovi?, Nina,Stanojkovi?, Tatjana,Sladi?, Du?an,Vuj?i?, Miroslava,Janovi?, Barbara,Joksovi?, Ljubinka,Trifunovi?, Sne?ana,Markovi?, Violeta
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p. 1679 - 1697
(2018/10/26)
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- Activation of anti-oxidant Nrf2 signaling by enone analogues of curcumin
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Inflammation and oxidative stress are common in many chronic diseases. Targeting signaling pathways that contribute to these conditions may have therapeutic potential. The transcription factor Nrf2 is a major regulator of phase II detoxification and anti-oxidant genes as well as anti-inflammatory and neuroprotective genes. Nrf2 is widespread in the CNS and is recognized as an important regulator of brain inflammation. The natural product curcumin exhibits numerous biological activities including ability to induce the expression of Nrf2-dependent phase II and anti-oxidant enzymes. Curcumin has been examined in a number of clinical studies with limited success, mainly owing to limited bioavailability and rapid metabolism. Enone analogues of curcumin were examined with an Nrf2 reporter assay to identify Nrf2 activators. Analogues were separated into groups with a 7-carbon dienone spacer, as found in curcumin; a 5-carbon enone spacer with and without a ring; and a 3-carbon enone spacer. Activators of Nrf2 were found in all three groups, many of which were more active than curcumin. Dose-response studies demonstrated that a range of substituents on the aromatic rings of these enones influenced not only the sensitivity to activation, reflected in EC50 values, but also the extent of activation, which suggests that multiple mechanisms are involved in the activation of Nrf2 by these analogues.
- Deck, Lorraine M.,Hunsaker, Lucy A.,Vander Jagt, Thomas A.,Whalen, Lisa J.,Royer, Robert E.,Vander Jagt, David L.
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supporting information
p. 854 - 865
(2017/12/13)
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- Including yinyin zuo of chalcone derivatives and use thereof
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The invention including yinyin zuo of chalcone derivatives and its application. As shown in general formula I including yinyin zuo of chalcone derivatives and their pharmaceutically acceptable salt, hydrate, solvate or prodrug has anti-tumor effect. The i
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Paragraph 0048; 0049
(2018/10/19)
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- Inhibiting Firefly Bioluminescence by Chalcones
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Chalcone refers to an aromatic ketone and an enone that constitutes the central core for various important biological compounds in drug discovery. Moreover, the firefly luciferase (Fluc) as the bioluminescent reporter has been widely used in life science
- Zhang, Huateng,Su, Jing,Lin, Yuxin,Bai, Haixiu,Liu, Jiaxiang,Chen, Hui,Du, Lupei,Gu, Lichuan,Li, Minyong
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p. 6099 - 6105
(2017/06/23)
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- A kind of including the secker niter zuo skeleton pyrazole nitro imidazole derivatives, preparation method and application thereof
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The invention discloses a pyrazole nitro imidazole derivative containing a secnidazole framework and a preparation method thereof and application. The structure of the pyrazole nitro imidazole derivative synthesized by secnidazole is shown as the formula (please see the formula in the specification), wherein R1 is selected from H, CH3, Br, CF3, OCH3, NO2, OCH2CH3, C1, F and I. The pyrazole nitro imidazole derivative has the obvious inhibiting effects on human hepatoma cells (HEPG2), human breast cancer cells (MCF-7), human cervical cancer cell lines (HeLa cells) and mouse melanoma cells (B16-F10), and therefore the pyrazole nitro imidazole derivative containing the secnidazole framework can be applied to prepare antineoplastic drugs.
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Paragraph 0030-0032
(2017/09/02)
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- A skeleton containing metronidazole pyrazole nitro imidazole derivatives, preparation method and application thereof
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The invention discloses pyrazol nitryl imidazole derivatives containing metronidazole frameworks, a preparation method and application of the derivatives. The structural formula of the pyrazol nitryl imidazole derivatives synthesized by metronidazole is s
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Paragraph 0032
(2018/03/01)
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- Design, synthesis and biological evaluation of pyrazolyl-nitroimidazole derivatives as potential EGFR/HER-2 kinase inhibitors
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A series of novel pyrazole-nitroimidazole derivatives had been arranged and evaluated for their EGFR/HER-2 tyrosine kinase inhibitory activity as well as their antiproliferative properties on four kinds of cancer cell lines (MCF-7, Hela, HepG2, B16-F10).
- Tao, Xiang-Xiang,Duan, Yong-Tao,Chen, Long-Wang,Tang, Dan-Jie,Yang, Meng-Ru,Wang, Peng-Fei,Xu, Chen,Zhu, Hai-Liang
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supporting information
p. 677 - 683
(2016/01/09)
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- Synthesis and in vitro biological evaluation of dihydroartemisinyl-chalcone esters
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A series of dihydroartemisinyl-chalcone esters were synthesized through esterification of chalcones with dihydroartemisinin (DHA). The hybrids were screened against chloroquine (CQ) sensitive (3D7) and CQ resistant (W2) strains of intraerythrocytic Plasmo
- Smit, Frans J.,Van Biljon, Ri?tte A.,Birkholtz, Lyn-Marie,N'da, David D.
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- Effective palladium-catalyzed hydroxycarbonylation of aryl halides with substoichiometric carbon monoxide
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A protocol for the Pd-catalyzed hydroxycarbonylation of aryl iodides, bromides, and chlorides has been developed using only 1-5 mol % of CO, corresponding to a pCO as low as 0.1 bar. Potassium formate is the only stoichiometric reagent, acting as a mildly basic nucleophile and a reservoir of CO. The substoichiometric CO could be delivered to the reaction from an acyl-Pd(II) precatalyst, which provides both the CO and an active catalyst, and thereby obviates the need for handling a toxic gas.
- Korsager, Signe,Taaning, Rolf H.,Skrydstrup, Troels
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supporting information
p. 2891 - 2894
(2013/04/10)
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- Scope and applicability of an expedient synthesis leading to polysubstituted 3-(carboxyphenyl)pyrroles
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A convenient three-step route toward a functionalized pyrrole building block for novel anti-inflammatory agents is reported. In contrast to previous strategies, the present approach focuses on inexpensive starting materials and application on a multigram
- Ullrich, Thomas,Ghobrial, Michael,Weigand, Klaus,Marzinzik, Andreas L.
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p. 1109 - 1119
(2008/02/01)
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- HISTAMINE H3 RECEPTOR AGENTS, PREPARATION AND THERAPEUTIC USES
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The present invention discloses novel compounds of Formula (I) or pharmaceutically acceptable salts thereof which have histamine-H3 receptor antagonist or inverse agonist activity, as well as methods and intermediates for preparing such compounds. In anot
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Page/Page column 24
(2010/11/24)
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- TPA-induced up-regulation of activator protein-1 can be inhibited or enhanced by analogs of the natural product curcumin
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The activator protein-1 (AP-1) family of transcription factors, including the most common member c-Jun-c-Fos, participates in regulation of expression of numerous genes involved in proliferation, apoptosis, and tumorigenesis in response to a wide array of stimuli including pro-inflammatory cytokines, growth factors, stress, and tumor promoters. A number of plant polyphenols including curcumin, a yellow compound in the spice turmeric, have been shown to inhibit the activation of AP-1. Curcumin is a polyphenolic dienone that is potentially reactive as a Michael acceptor and also is a strong anti-oxidant. Multiple activities reported for curcumin, including inhibition of the stress-induced activation of AP-1, have been suggested to involve the anti-oxidant properties of curcumin. In the present study, a library of analogs of curcumin was screened for activity against the TPA-induced activation of AP-1 using the Panomics AP-1 Reporter 293 stable cell line which is designed for screening potential inhibitors. Numerous analogs were identified that were more active than curcumin, including analogs that were not anti-oxidants and analogs that were not Michael acceptors. Clearly, anti-oxidant activity or reactivity as a Michael acceptor is not an essential feature of active compounds. In addition, a number of analogs were identified that enhanced the TPA-induced activation of AP-1. The results from screening were confirmed using BV-2 microglial cells where curcumin and analogs were shown to inhibit LPS-induced COX-2 expression; analogs identified as more potent than curcumin in the screening assay were also more potent than curcumin in preventing COX-2 expression.
- Weber, Waylon M.,Hunsaker, Lucy A.,Gonzales, Amanda M.,Heynekamp, Justin J.,Orlando, Robert A.,Deck, Lorraine M.,Vander Jagt, David L.
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p. 928 - 940
(2007/10/03)
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- Method and compounds for cancer treatment utilizing NFkB as a direct or ultimate target for small molecule inhibitors
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A method is described for cancer treatment through NFκB inhibition. NFκB is a direct or ultimate target for small molecule inhibitors. These small molecule inhibitors are aimed at suppression of NFκB directly or by indirect suppression of IKK, SFK kinases, or other upstream kinases. The present invention includes small molecule inhibitors comprising three, five, and seven carbon unsaturated spacers having one or two carbonyls, flanked by substituted aryl rings. The small molecule inhibitors can be symmetrical or unsymmetrical.
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Page/Page column 4; sheet 3
(2008/06/13)
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- Anti-oxidant activities of curcumin and related enones
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The natural product curcumin (diferuloylmethane, 1,7-bis(4-hydroxy-3- methoxyphenyl)-1,6-heptadiene-3,5-dione), obtained from the spice turmeric, exhibits numerous biological activities including anti-cancer, anti-inflammatory, and anti-angiogenesis activities. Some of these biological activities may derive from its anti-oxidant properties. There are conflicting reports concerning the structural/electronic basis of the anti-oxidant activity of curcumin. Curcumin is a symmetrical diphenolic dienone. A series of enone analogues of curcumin were synthesized that included: (1) curcumin analogues that retained the 7-carbon spacer between the aryl rings; (2) curcumin analogues with a 5-carbon spacer; and (3) curcumin analogues with a 3-carbon spacer (chalcones). These series included members that retained or were devoid of phenolic groups. Anti-oxidant activities were determined by the TRAP assay and the FRAP assay. Most of the analogues with anti-oxidant activity retained the phenolic ring substituents similar to curcumin. However, a number of analogues devoid of phenolic substituents were also active; these non-phenolic analogues are capable of forming stable tertiary carbon-centered radicals.
- Weber, Waylon M.,Hunsaker, Lucy A.,Abcouwer, Steve F.,Deck, Lorraine M.,Vander Jagt, David L.
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p. 3811 - 3820
(2007/10/03)
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- INHIBITORS OF HISTONE DEACETYLASE
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The invention provides compoods and methods for treating cell proliferative- diseases. The invention provides new inhibitors of histone deacetylase enzymatic activity, compositions of the compounds comprising the inhibitors and a pharmaceutically acceptable carrier, excipient, or diluent, and methods of using the compounds to inhibit cellular proliferation in vitro and therapeutically.
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- New bis(chalcones) and their transformation into bis(pyrazoline) and bis(pyrazole) derivatives
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The reaction of bis(chalcones) 1a-d and bis(chalcone) tetrabromo derivatives 3a-d with hydrazine hydrate gave bis(pyrazolines) 4a-d and bis(pyrazoles) 5a-d, respectively. Bis(pyrazoles) 5e,f bearing hydroxyphenyl substituents have been prepared from the r
- Pinto, Diana C. G. A.,Silva, Artur M. S.,Cavaleiro, Jose A. S.,Elguero, Jose
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p. 747 - 755
(2007/10/03)
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- Inhibitors of histone deacetylase
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The invention relates to the inhibition of histone deacetylase. The invention provides compounds and methods for inhibiting histone deacetylase enzymatic activity. The invention also provides compositions and methods for treating cell proliferative diseases and conditions.
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- Chemical adsorbate compound, organic film, liquid crystal alignment film, and liquid crystal display device utilizing the chemical adsorbate compound
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A novel chemical adsorbate compound capable of forming a monomolecular thin film is provided. The chemical adsorbate compound is transparent and stable in the visible light range, and has a photosensitive group which causes a photochemical reaction in the
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- Cytotoxic N-[4-(3-aryl-3-oxo-1-propenyl)phenylcarbonyl]-3,5-bis(phenylmethylene)-4- piperidones and related compounds
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A series of 4-carboxychalcones 1 were prepared and coupled to 3,5-bis(phenylmethylene)-4-piperidone (2) giving rise to a novel series of N-[4-(3-aryl-3-oxo-1-propenyl)phenylcarbonyl]-3,5-bis(phenylmethylene)-4- piperidones (3). Molecular simplification of the amides 3 led to the formation of the corresponding N-(3-aryl-1-oxo-2-propenyl)-3,5-bis(phenylmethylene)-4-piperidones (4). A cytotoxic evaluation of the compounds in series 1-4 utilized murine P388 and L1210 cells as well as human Molt 4/C8 and CEM T-lymphocytes. In general, the compounds displayed significant toxicity; the IC50 values of 54% of the enones were less than 10 μM when all four screens were considered and less than 1 μM for all members of series 3 in the P388 assay. Various correlations were established between the potencies of the compounds in series 1, 3 and 4 and the Hammett σ, Hansch π and molecular refractivity constants of the aryl substituents. Several torsion angles and interatomic distances of five representative compounds in series 3 and 4 were determined by X-ray crystallography, some of which contributed to the observed bioactivity. The marked cytotoxicity and lack of murine toxicity of most of the compounds described in this study, as well as their selective toxicity towards different tumour cell lines, revealed that development of the enones 2-4 as novel candidate antineoplastic agents should be pursued.
- Dimmock, Jonathan R.,Jha, Amitabh,Zello, Gordon A.,Quail, J. Wilson,Oloo, Eliud O.,Nienaber, Kurt H.,Kowalczyk, Earl S.,Allen, Theresa M.,Santos, Cheryl L.,De Clercq, Erik,Balzarini, Jan,Manavathu, Elias K.,Stables, James P.
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p. 961 - 972
(2007/10/03)
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- Pyridine derivative
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A pyridine derivative represented by the following formula: STR1 where R1 and R2 are as defined in the specification, or a salt thereof. These compounds directly or indirectly act on neuronal cells in vivo and are effective in the am
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- Inhibition of the EGF-stimulated cellular proliferation of ER 22 cells by hydroxybiphenyl derivatives
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Several series of hydroxybiphenyl compounds substituted by a hydrophobic group (tert-butyl or phenyl) and bearing a free or protected carboxylic moiety were synthesized. The compounds were tested for their ability to inhibit the intrinsic tyrosine protein
- Million,Boiziau,Parker,Tocque,Roques,Garbay
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p. 4693 - 4703
(2007/10/03)
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- Retinobenzoic Acids. Structure-Activity Relationships of Chalcone-4-carboxylic Acids and Flavone-4'-carboxylic Acids
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The structure-activity relationships of (E)-chalcone-4-carboxylic acids, which are retinoidal benzoic acids represented by R-Ph-X-Ph-COOH (4, X=-COCH=CH-), are discussed on the basis of differentiation-inducing activity on human promyelocytic leukemia cells HL-60.The activity was increased by the substitution of a bulky alkyl group(s) (R), and among such compounds, (E)-4-benzoic acid (Ch55) and (E)-4-benzoic acid (Ch80) are several times more active than retinoic acid.Though the stable conformer of chalcone derivatives is linear (s-cis form), the conformationally restricted analogue 4-(6,7,8,9-tetrahydro-6,6,9,9-tetramethyl-4H-4-oxonaphthopyran-2-yl)benzoic acid (Fv80) is more active than Ch80.While the effect of introduction of an oxygen atom varied, 4-benzoic acid (Re80), regarded as a derivative of Ch80 with two additional hydroxyl groups, has very strong activity.
- Kagechika, Hiroyuki,Kawachi, Emiko,Hashimoto, Yuichi,Shudo, Koichi
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p. 834 - 840
(2007/10/02)
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